Should you work for yourself or someone else?

More women are choosing to work for themselves, but how do you know if it’s right for you? Career changer Jacqui Ooi shares what she’s learned from stepping out on her own, and interviewing many women who’ve made similar moves on the What She Did Next podcast.

When you’re thinking about your next career move, one option that is more prevalent than ever is working for yourself.

According to the latest stats, around one in eight working women in Australia are self-employed and women now make up a third of all Australian business owners after a steady increase over the past two decades.

For many women, starting their own business is borne out of a need (or desire) for more flexible work hours and it’s a choice that women tend to make later in life, with almost half of women business owners in Australia aged 40-54.

Interestingly, the data also shows that self-employed women have higher job satisfaction than other female workers. And side note: women-owned businesses are good for other women! They typically employ more women and have structures in place that support flexibility and other needs of working parents.

So on paper, there’s a lot to love about working for yourself… but how do you know if being self-employed is right for you?

The perks and challenges

As someone who has been self-employed for the past three years, and interviewed many women who’ve made the leap to freelance life or started a business on the What She Did Next podcast, I know there are a few misconceptions out there about working for yourself – which could hold you back from considering it as a real possibility OR give you a rose-coloured view that isn’t rooted in reality.

The truth is, it’s not as scary as you might think or as rosy as you might imagine. But it is certainly doable and there’s more support for self-employed women than ever before.

Here’s what you need to know.

Will being self-employed give me the flexibility I dream of?

The answer is yes, it most certainly can… but not necessarily straight away and it also depends on your business type and personality. Getting any new venture off the ground takes time and hard work, but if your goal is to build a business that fits in with your life, not vice versa, you will learn through trial and error how to make that happen.

For example, if you’re a freelancer or sole business owner doing everything yourself, that can feel like a lot at first, but you’ll soon learn what can be outsourced and how to structure your business in a way you enjoy and that feels manageable.

It doesn’t necessarily mean working less hours, at least at the start, but there is something freeing about being able to create your own work schedule… so you can commit to that lunchtime yoga class or take that 10am doctor’s appointment or do the school run with your kids or book that holiday without having to check with anyone!

From my own experience, I’ve also enjoyed knowing that any busy periods are of my own doing and I can turn them off when I need to, rather than being stuck in a relentless churn outside of my control.

You may need to do a bit of honest self-reflection too, to avoid carrying over any bad habits from your current work situation. For example, if you have trouble setting boundaries and you’re prone to taking on too much work, that can still be a problem as a self-employed person. Taking steps to address that (or any other issues that are more about you than your work environment) is critical to prevent burnout and ensure the flexibility you crave.

Is being self-employed financially risky?

The million-dollar question! Not surprisingly, one of the biggest worries people have about giving up a ‘secure’ job to become self-employed is the fear of giving up their regular income. When you’ve worked for someone else your entire life and become used to a certain amount of money landing in your bank account at the same time each week or month, the idea of switching to an inconsistent or potentially lower income stream (at least initially) can feel quite frightening.

And of course, we all need a certain level of income to survive and thrive. So you don’t want to make any rash decisions without first thinking through what you actually need to be financially secure each month and have a plan in place to manage the transition.

That might involve having some savings set aside, or taking a part-time or contract role for a period of time. You might have a spare room you could rent out (one of our pod guests did this to generate some income while getting her consultancy off the ground) or you could investigate whether you’re eligible for financial assistance through a government program such as NEIS or a start-up grant.

You can be as creative as you like when it comes to the money side of things, but the point is, there are ways you can still earn an income or have a financial buffer in place as you transition to self-employment, which will take a lot of the stress out of the move.

TIP! If you’re looking to buy a house, you will likely discover (as we did) that most banks require at least two years of income as a self-employed person to consider you for a loan, so bear this timing in mind.

Aside from the practicalities, you do need to get comfortable with the fact that your income may not be consistent – you may have big months, slower months and everything in between. (Equally, you may end up earning MORE than you were in your salaried role. We get so focused on the ‘secure’ part of being on a fixed income that we can overlook its Iimitations.)

In short, there are steps you can take to manage the financial risk of shifting to self-employment, but the mindset shift can be the biggest challenge of all. What I’ve enjoyed about that shift though is how much more financially conscious and literate I’ve become. I pay so much more attention now to the ins and out of my money, and I’ve learned so much about ways to take control of your money and feel more financially secure as a result.

Isn’t it boring/lonely working for yourself?

It can be! Again, I would say this very much comes down to your personality and how much ‘people time’ you need. Also how do you like to work – are you someone who likes to bounce ideas off other people or do you prefer being head-down getting on with things? Or a mix of both?

How reliant are you on work for your social life? Do you like heading out for after-work drinks or team lunches? If you’ve always worked in big organisations and enjoyed the buzz and camaraderie, it could be quite a culture shock to transition to working for yourself.

Having said that, there are lots of ways – especially post-COVID – to create a work set-up that fits your needs:

  • You might want to join a co-working space a day or two a week, so you can escape the house and meet other people.
  • You might want to join an online community or local business group where you can connect and learn from other women working for themselves.
  • You might build a team around you, if not full-time then freelance. At different times, I’ve had a bookkeeper, a social media manager, a digital marketing specialist and an associate producer… other women I know have VAs or online business managers helping them.

There are so many supports out there now for women stepping out on their own, at both a practical and mindset level. Even listening to podcasts can make you feel less alone and spark all sorts of ideas for your own venture.

What work could I actually do?

For many women, it’s not knowing what you want to do next that can be the biggest barrier of all. There’s a whole process you can go through to figure this out (which I teach in our online course) but suffice to say, the options available to us now are almost endless, thanks in large part to the massive shifts in technology we’ve seen in recent decades, the ease of online study, and the proliferation of information and support for women who are self-employed.

If you quite enjoy the work you do, then a simple option would be to keep doing that but in a freelance or contract capacity, using existing networks to help you get started. That doesn’t mean you have to stick with it forever. But it will give you a taste of whether self-employed life is for you without having to retrain or upskill straight away.

If you want to do something different, think about:

  • What skills do you have that solve a problem for someone else?
  • What lived experience do you have that could make your offering uniquely you?
  • What do you actually want to put out there in the world? What matters to you? What lights you up? What difference do you want to make?

Also think about how you can sell what you know rather than what you do. You might be at a point in your career where your knowledge and understanding of an industry is of value in a whole range of ways, so what can you offer that will be of benefit to organisations or individuals in that industry?

Like I said, exploring what else is out there for you is a process and it takes time, but you don’t have to have it all figured out before you make a move. In fact, taking action – however imperfect or small it might be – is a critical first step to working it out.

Keen to know more?

If you’re after some inspiration from other women who work for themselves, I can recommend some of our podcast episodes:

  • Emma McMillan became a freelance copywriter and copy coach after leaving her teaching career.
  • Tamara Pitelen became a sustainability consultant after leaving her media career.
  • Evie Farrell became a tour guide and runs her own travel company specialising in group trips for women, and for mums and kids, after leaving her PR career.

I also love Marisa’s story of leaving her career in customer service to start her own floristry business… with a difference!

The upshot is, making the leap to self-employment is like starting any new job – you need to be prepared to go through a learning period and feel like a fish out of water for a while. You’ll be discovering new things about yourself and doing things you’ve never done before. You’ll be figuring out a different way of earning an income and wearing many hats along the way. And while it can all feel big and overwhelming at times, there is plenty of support out there to tap into, so you don’t have to go it alone.

Jacqui Ooi is the founder of What She Did Next, a podcast and online learning platform for women who want to make a career change. A two-time career changer herself and an experienced mentor, she teaches practical strategies to help women navigate their career change journey.

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